1,1'-Carbonyldiimidazole → (R)-N-(1-(3,4-dichlorophenyl)ethyl)-2-(2-ethoxypyridin-4-ylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

Participants

Reaction Steps

A vial was charged with 185 (0.105 g, 0.553 mmol), CDI (0.0896 g, 0.553 mmol) and DCM (2 mL) and stirred for 30 min. To the solution was added 186 (0.150 g, 0.553 mmol) and DIPEA (0.193 ml, 1.11 mmol) and the resulting reaction stirred for 3 d. The reaction was washed with brine (4 mL), and the organic phase concentrated and loaded on to a preparative SiO2 plate (1.0 mm thickness) which was developed with EtOAc/MeOH (95:5) and eluted to afford 0.038 g (13%) of I-35: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.96 (d, 1H), 7.73 (s, 1H), 7.44 (m, 1H), 7.35 (d, 1H), 7.29 (m, 1H), 7.20 (m, 1H), 6.95 (m, 1H), 5.40 (d, 1H), 5.00 (m, 1H), 4.49 (s, 1H), 4.36 (q, 2H), 3.68 (m, 2H), 2.72 (d, 2h), 1.49 (d, 3H), 1.39 (t, 3H); m/z (APCI-pos) M+1=487.2.

Provenance & Evidence